140 Tripp Road Woodstock, CT $ 375,000
140 Tripp Road
$ 375,000
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140 Tripp Road

Woodstock, CT, 06281
$ 375,000
Bedrooms2 Baths1.0 Sq 1,274

Monthly Estimate*

$ 2,309

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Single Family Home for sale in Woodstock, CT

for $375,000 with 2 bedrooms and 1 full bath. This 1,274 square foot home was built in 1840 on a lot size of 0.4.

This residence offers a rare opportunity to inhabit a piece of Woodstock's history. Originally commissioned in 1840 and crafted by William Hammond of Woodstock Hill, the structure served as the Harrisville District School, educating the youth of Pomfret, Thompson, and Woodstock for eight decades. After closing its doors as a place of learning in 1920, it has been meticulously preserved and thoughtfully expanded, remaining under the stewardship of its current owners for the past 28 years. The home's architecture is a marriage of the original 19th-century brickwork and contemporary refinements. Access is granted via two entrances: the original exterior school stairs from Harrisville Road or the more everyday kitchen entry located off the driveway and deck. The dine-in kitchen features custom cabinetry, a generous kitchen island, and a dedicated wood stove. Sliding glass doors transition seamlessly to the back patio, inviting the outdoors in. Occupying the footprint of the original one-room schoolhouse, the living room features a fireplace mantel and wood stove anchoring the space, it brings a profound sense of warmth and character that is felt during any season. The main level is completed by a versatile reading nook or home office and a full bath featuring both a jetted soaking tub and a separate stall shower. Housed on the second floor are the primary and secondary bedroom. The post and beam garage is a significant asset to the property, this substantial building currently serves as a garage and workshop. Designed with future versatility in mind, the structure features a fully floored upper level and was engineered for an easy conversion into a three-bay garage. The grounds are curated for relaxation and entertainment. A fragrant lilac tree greets visitors at the deck, while a gazebo and a paver patio provide additional spaces for outdoor dining and enjoyment. Modern needs are addressed with a dedicated pad for RV or boat storage, complemented by raised garden beds ready for summer fruits and veggies. 140 Tripp Rd. was loved first as a school and then as a family residence. It is waiting for a new owner who will continue to care for its unique features and history.

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Single Family Contingent

Price

$ 375,000

Bedrooms

2

Full Bath

1

Property Type

Single Family

Taxes

$ 3,713

Style

Lot Size

0.4

Year Built

1840

Town/City

Woodstock

MLS | Web ID

24169479

Features
General
Zoning 0
Neighborhood Harrisville
County Windham
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract
Acres 0.4
Directions From I-395N: Exit 45/To Kennedy Dr. Right to Kennedy Dr. Left onto Rte. 44/Pomfret St. Right onto Sabin St. Left onto Tripp Rd. Property is on your Right.
High School Woodstock Academy
City Woodstock
Elementary School Woodstock
Sq Ft Total 1274
DOM 3
Year Built 1840
Style Cape Cod Other
Year Built Source Public Records
Energy Features Active Solar Ridge Vents Storm Doors Thermopane Windows
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Interior
Cooling System Window Unit
Total Rooms 5
Basement Description Full Unfinished Interior Access Concrete Floor Full With Hatchway
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Exterior
Water Source Public Water Connected
Lot Description Corner Lot Treed Level Lot Sloping Lot
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* Excluded Features
List By
Heather Sawyer

Listing Agent

William Pitt Sotheby's Int'l

Broker

hsawyer@wpsir.com

Email

Affordability Calculator

$2,618
Per Month
88%
12%
0%
Monthly Principal & Interest
$2,309
Monthly Property Taxes
$309
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3041817 Elementary School
1186813 Middle School
Woodstock Academy High School High School
Pricing History
DatePricePrice ChangeDescription
5/11/2026$375,000 Listed Price

Map


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140 Tripp Road, Woodstock, CT, 06281 is a Single Family Home for sale at $375,000 with 1,274 sqft and a lot size of 0.4. 140 Tripp Road has 2 bedrooms, 1.0 baths, and was built in 1840. The property's zip code is 06281 which is in Woodstock, CT